Chatham Sailboat Rentals

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434 Ridgevale Rd
Chatham, MA 02633
Sailboat rentals, kayaks, stand-up paddle boards, lessons and tours in Chatham, Massachusetts, on the kid-friendly Ridgevale Beach. Family owned & operated for over 50 years in conjunction with the Ridgevale Beach Snack Bar, Chatham Sailboat Rentals offers water activities for all skill and age levels to be enjoyed on Buck's Creek and Nantucket Sound.

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4.56 reviews
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Alexis W.
8/7/2025

Eric was so kind to take us out on a last min addition to his day. He was fun to talk with about Chatham, sailing and the tides. Definitely rent a sailboat or take a lesson from him/business.

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Jessica K.
9/11/2021

Absolutely amazing experience. Everyone was lovely and the boats were so much fun. We went back for a second time

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Tina M.
7/13/2020

I wish communication was better so that we could plan. Did not realize water would be choppy for SUP and younger kids. Staff was super kind and understanding

Mark N.
10/2/2019

Wonderful experience, I rented a hobie cat and my wife rented a kayak for a few hours. We were very pleased with the rental and the equipment. We wanted to go on a Tuesday, but was told the...

Mike B.
6/24/2020

Friendly service, great location. Pricing is also competitive (even better than a few I've seen). I've rented at a few places on the Cape and this will probably be my go to spot. It's a good mix...

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